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Whitepaper

What You’ll Learn

This whitepaper answers each one in plain language. A glossary and links to Microsoft's own documentation will help everyone involved in a licensing decision to start from the same facts.

THE PROBLEM

Why One Microsoft Purchase Involves Four Separate Questions

A Microsoft licensing decision can involve four purchasing vehicles, five major product families, and five pricing models. In May 2026 Microsoft added Microsoft 365 E7, its first new enterprise tier since E5 launched in 2015. Each choice has its own eligibility rules. Together these choices fall into four separate questions that can be answered one at a time.

THE BLIND SPOT

Eligibility Rules Narrow the Options Before Price Comes Up

Microsoft 365 Business plans are capped at 300 users, and organizations under roughly 2,400 seats are increasingly told at renewal that a new Enterprise Agreement (EA) is unavailable. Their alternatives include the Microsoft Customer Agreement for Enterprise (MCA-E) and purchasing through a Cloud Solution Provider (CSP). A comparison table in the whitepaper shows which agreements fit which organization sizes.

THE MODEL

Why Answering the Questions Separately Produces Clearer Decisions

Separating the purchasing vehicle from the product tier and the pricing model makes each part easier to evaluate on its own. The whitepaper covers Microsoft 365, Dynamics 365, Power Platform, Azure, and Windows Server. It also explains the five pricing models behind them, using examples such as shift-work terminals priced per device and servers priced per core.

THE NEXT STEP

Applying the Four Questions to Your Own Microsoft Environment

Timing is the fourth question. A Gartner survey reported by TechTarget found 4% of IT and AI leaders highly likely to upgrade to Microsoft 365 E7 within the year and another 16% somewhat likely. Before your next renewal conversation, ask which of the four questions is still open. DCG's licensing team can work through that question with you.

Who Should Read This Whitepaper?

This whitepaper is written for teams that share one Microsoft licensing decision:

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  • Procurement and Sourcing Leaders who compare purchasing vehicles and explain the final choice to legal and leadership
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  • IT and Infrastructure Leaders who match Microsoft 365, Azure, and Windows Server licensing to what the environment runs
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  • Finance and Budget Leaders who need to see what drives each Microsoft bill, including per-user seats and Azure consumption
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  • CIOs, CFOs, and Procurement Executives who are weighing an EA renewal, an MCA-E transition, or a CSP purchase
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  • Licensing and Software Asset Managers who check feature usage against what the organization has licensed
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  • Technology Leaders who are deciding whether Microsoft 365 E5 or E7 fits their AI agent plans

Michael Richardson

Most Microsoft environments carry more cost than they should. Licenses go underutilized, support contracts deliver ticket queues instead of senior expertise, and cloud infrastructure built for one initiative rarely gets revisited. Michael has spent his career fixing exactly that. 

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